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Electrochemical Synthesis of Isoxazolines: Method and Mechanism

preprint
submitted on 22.12.2020, 23:07 and posted on 24.12.2020, 04:55 by Samuel David Lee Holman, Neal Fazakerley, Darren poole, Diane M. Coe, Leonard Berlouis, Marc Reid
An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline via an electrochemically enabled regio- and diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ reaction monitoring methods compatible with electrochemistry equipment have also been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time-course) modeling and density functional theory support a stepwise, radical-mediated mechanism, and discounts hypothesized involvement of closed shell [3+2] cycloaddition pathways.

Funding

Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation

Engineering and Physical Sciences Research Council

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History

Email Address of Submitting Author

marc.reid.100@strath.ac.uk

Institution

University of Strathclyde

Country

United Kingdom

ORCID For Submitting Author

0000-0003-4394-3132

Declaration of Conflict of Interest

No conflict of interest.

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